Synthesis of N-(3-Azido-2-hydroxypropyl), N-(3-Phthalimido-2-hydroxypropyl) and N-(3-Amino-2-hydroxypropyl) Derivatives of Heterocyclic Bases

[img]PDF - Authorized users only
Language: English
216Kb
Title:Synthesis of N-(3-Azido-2-hydroxypropyl), N-(3-Phthalimido-2-hydroxypropyl) and N-(3-Amino-2-hydroxypropyl) Derivatives of Heterocyclic Bases
Creators:
Spassova, Maria
Dvořáková, Hana
Holý, Antonín
Buděšínský, Miloš
Masojídková, Milena
Journal or Publication Title:
Collection of Czechoslovak Chemical Communications, 59, 5, pp. 1153-1174

Abstract

<p>Alkylation of heterocyclic bases with azidomethyloxirane (<i>I</i>) under basic catalysis with potassium or cesium carbonate afforded <i>N</i>-(3-azido-2-hydroxypropyl) derivatives <i>II</i>. Hydrogenation of these compounds over palladium on carbon gave the corresponding 3-amino-2-hydroxypropyl derivatives <i>III</i>. The same compounds <i>III</i> were prepared by alkylation of heterocyclic bases with phthalimidomethyloxirane (<i>VII</i>) in the presence of cesium carbonate and subsequent reaction of the formed <i>N</i>-(3-phthalimido-2-hydroxypropyl) derivatives <i>VIII</i> with hydrazine. The phthalimido derivatives <i>VIII</i> are easily hydrolyzed already in weakly alkaline aqueous medium to give 9-[3-(<i>o</i>-carboxybenzoylamino)-2-hydroxypropyl] derivatives <i>IX</i> and <i>X</i>.

Title:Synthesis of N-(3-Azido-2-hydroxypropyl), N-(3-Phthalimido-2-hydroxypropyl) and N-(3-Amino-2-hydroxypropyl) Derivatives of Heterocyclic Bases
Creators:
Spassova, Maria
Dvořáková, Hana
Holý, Antonín
Buděšínský, Miloš
Masojídková, Milena
Divisions:Life and Chemical Sciences > Institute of Organic Chemistry and Biochemistry > Collection of Czechoslovak Chemical Communications
Journal or Publication Title:Collection of Czechoslovak Chemical Communications
Volume:59
Number:5
Page Range:pp. 1153-1174
ISSN:0010-0765
E-ISSN:1212-6950
Publisher:Institute of Organic Chemistry and Biochemistry
Related URLs:
URLURL Type
http://dx.doi.org/10.1135/cccc19941153UNSPECIFIED
ID Code:534
Item Type:Article
Deposited On:06 Feb 2009 17:01
Last Modified:06 Feb 2009 16:01

Citation

Spassova, Maria; Dvořáková, Hana; Holý, Antonín; Buděšínský, Miloš; Masojídková, Milena (1994) Synthesis of N-(3-Azido-2-hydroxypropyl), N-(3-Phthalimido-2-hydroxypropyl) and N-(3-Amino-2-hydroxypropyl) Derivatives of Heterocyclic Bases. Collection of Czechoslovak Chemical Communications, 59 (5). pp. 1153-1174. ISSN 0010-0765

Repository Staff Only: item control page